Dimethoxymethane → HCID 18351832, compound

HRID 430765Notes

Reaction equation

HRID 430765 reaction equation
[OH:1][CH2:2][CH:3]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:5]=2[O:4]1.[CH3:15][O:16][CH2:17]OC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH3:15][O:16][CH2:17][O:1][CH2:2][CH:3]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:5]=2[O:4]1

Participants

6

Reactant 4

HCID 8020DimethoxymethaneHCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 18351576HCID 18351576, compound

Product 1

HCID 18351832HCID 18351832, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-dihydro-2-hydroxymethyl-3-oxo-7-methoxybenzofuran (1.79 g) and dimethoxymethane (10 ml) were dissolved in dichloromethane (25 ml) and phosphorus pentoxide (3.47 g) was added to the obtained solution, followed by stirring the resulting solution at room temperature for 3.5 hours. The reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layers were combined and washed with water and with saturated brine, followed by drying over magnesium sulfate. Magnesium sulfate was removed by filtration and the solvent was evaporated off. The residue was purified by column chromatography (solvent: n-hexane/ethyl acetate=1/1) to obtain the desired compound (912 mg, yield: 58%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and with saturated brine
  3. dry with materialby drying over magnesium sulfate
  4. customMagnesium sulfate was removed by filtration
  5. customthe solvent was evaporated off
  6. customThe residue was purified by column chromatography (solvent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-86e783baf43741129f9fbee3fc309a9a
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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